The Art Of Wearing Cufflinks


There are few things I like more than a well-dressed man.

Blame it on Gene Kelly and his grace while dancing in suit-and-tie for Singin’ In The Rain, or on my father who was dressed-and-pressed six (and sometimes seven) days of the week, and who criticized my dates for picking me up in merely shirt, tie… and jeans.

Blame it on the assault of casualness that came increasingly with the sixties, seventies, eighties, nineties and into the new millennium, when a girl is gawked at but can’t find a match when she just feels like dolling-up.

Blame it on whatever you like; well-cut suits are sexy, and cufflinks are the quintessence of men’s style, the mark of a man who has enough sensitivity considering his attire to find, select and pair a dress shirt with French cuffs and cufflinks.

Men’s dress shirts with studs and cufflinks fell out of fashion with the Industrial Revolution, when dress shirts became cheap and quick to produce with buttons already affixed. Those requiring cufflinks and studs to hold the shirt together are now relegated to formal events and special occasions when such men’s jewelry could be shown off, keeping the best for the best, since they were expensive.

Today, cufflinks are available for almost any price, selling for as little as a few dollars at antique shows and vintage/used clothing stores to thousands of dollars from high-end designers and jewelers. And, with designs as classic or as crazy as you can imagine, these pieces are the perfect expression of your unspoken elegance, style, wit or charm.

Buying Cufflinks

With so many different styles available and the price range so broad, it’s not hard to find cufflinks that suit your style. Vintage and used clothing stores are sometimes the most fun, since you’re likely to afford several pairs of unique and very beautiful cufflinks.

Novelty cufflinks are fun, especially if they express unknown parts of your personality. Do try to add some variety, though, since the idea is to express subtly those hidden parts of yourself.

Pictured: Circle Patterned Noak Cufflinks, by BOSS Black, $55

Size matters, too: if you’re a big, broad man, choose chunky pieces that your large size can carry off. More slender guys should look for medium to smaller cufflinks that will accentuate their build, and should stay away from bigger pieces that will only weigh down their smaller wrists and shoulders.

Pictured: Square Loyce Cufflinks, by BOSS Black, $84

Wearing Cufflinks

French-cuffed shirts have four sets of buttonholes on each cuff, allowing cufflinks to slip through and fasten. The more formal style is a ‘kissing cuff,’ in which the cuffs are paired together and fastened through with cuff edges pointing out. Though these look best with barbell, link or wrap-around cufflinks that show off on both sides, many men use the more common post cufflinks.

If you choose to wear post-style cufflinks with a ‘kissing cuff,’ be sure to close the post on the inside of the cuff, so the design shows when your arm hangs down.

Pictured: Check Blue Union Link, by Würkin Stiffs, $85

Less formal but still classy is the cylinder cuff: wrap the cuff around your wrist and overlap the front and back cuffs to form a cylinder. Push the cufflinks through the buttonholes such that the cufflink design sits on the outside; close the post inside the shirt.

Shirts should be well-fitted—especially in sleeve length, and most particularly when worn with a suit jacket. Sleeves should hit about a quarter-of-an-inch below the wrist when your arm is hanging down; have a tailor or knowledgable representative measure you to ensure you find the right length. And, as with any dress shirts, try them on before buying since some cuts will hang shorter or longer, despite the stated length.

Pictured: Multi Plaid Orange Union Link, by Würkin Stiffs, $85

Though more traditional men like my dad might not approve, cufflinks remain elegant when worn more casually without a tie and jacket—and even paired with a well-cut pair of jeans. Bear in mind that it is especially important to match them well: shirt and cufflinks should match or contrast in color, and all metals you’re wearing should be the same (gold cufflinks with gold belt buckle). Novelty cufflinks break the rules in general; so, if you’re wearing them, you have more leeway to flout convention—within reason, of course, or you’ll likely just look silly.


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